Multicomponent Synthesis of 3-Heteroarylpropionic Acids

Abstract

A four component one-pot procedure (4-MC) was developed to assemble 3-heteroarylpropionic acids from commercially available materials. This new methodology affords the title compounds in high yields and without the use of chromatography. [reaction: see text]

(2-Pyridyl)phenyl methanol: a new reagent for metal-free reduction of nitro aromatic compounds

“…It is likely that thermal decomposition of the isoxazole 21 prevails in these conditions, showing its reactivity as a masked acetate. 31 Nucleophilic attack of the alcohol 1 on the C-5 carbon atom of the isoxazole ring and subsequent ring opening gave the acetate 22.…”

Reaction of 5-(1-bromo-2-aryl-vinyl)-3-methyl-4-nitro-isoxazoles and 1,3-dicarbonyl compounds

“…1). [1][2][3][4][5][6][7][8][9][10] Compounds 1 can be readily prepared from commercially available 3,5-dimethyl-4-nitro-isoxazole and aromatic aldehydes. 4 It has been shown that compounds 1 can be considered as cinnamate equivalents where the 4-nitro-isoxazole core can be hydrolyzed to give a carboxylate.…”

“…4 It has been shown that compounds 1 can be considered as cinnamate equivalents where the 4-nitro-isoxazole core can be hydrolyzed to give a carboxylate. 2,3,8,11 It is noteworthy that compounds 1 have enhanced reactivity compared to cinnamates due to the conjugation of the nitro group at position C-4 of the isoxazole core. Furthermore, compounds 1 have two electrophilic centers that can be selectively reacted.…”

“…1). [1][2][3]8,11 As part of our programme of research devoted to the design and preparation of novel polyfunctional scaffolds 1-10 we considered the preparation of compounds 2 (Fig. 1).…”

Preparation of functionalised monobactams from pyridones

“…As a part of our ongoing studies on the generation of chemical diversity using aromatic heterocycles, [7][8][9][10][11][12] we envisaged a novel synthesis of monobactams starting from commercially available 2-pyridones (Scheme 1). 2-Pyridones possess a low degree of aromaticity, and for this reason, they often have been employed as dienes in Diels-Alder reactions.…”